- Synthesis of isomeric isoxazolopyridinones
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Reaction of 4-methylamino-5,6-dihydropyridinone with acetyl chloride yielded exclusively the 3-acetyl derivative. When the methylamino group of the latter was removed by alkaline hydrolysis, a mixture of two hydroxy derivatives was formed. Those cyclized upon treatment with hydroxylamine exclusively to the isoxazolo[4,5-c]pyridinone, whereas the 4-methylamino analogue yielded, depending on pH, mainly the isoxazolo[4,3-c]pyridinone or the isoxazolo[4,5-c]pyridinone. The configurations of the latter compounds were established by NMR experiments.
- Weis, Robert,Schweiger, Klaus,Fabian, Walter M. F.
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- 4-Hydroxy-6,6-dimethyl-5,6-dihydro-2(1H)-pyridinethione and -one and the Corresponding Tautomers
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The tautomers, 4-hydroxy-5,6-dihydro-6,6-dimethyl-2(1H)-pyridinethione (1) and 6,6-dimethyl-2-thioxo-4-piperidone (2) resp., and 4-hydroxy-5,6-dihydro-6,6-dimethyl-2(1H)-pyridone (9) and 6,6-dimethyl-2,4-piperidinedione (10) resp. were synthesized by hydrolysis of 4-amino-5,6-dihydro-6,6-dimethyl-2(1H)-pyridinethiones (4,5) and -ones (11,12). 1,2 and 9,10 undergo an aminolysis in amines to the corresponding 4-aminodihydro-2(1H)-pyridinethiones 4,5 and -ones 11, 12 resp. - Keywords: 6,6-Dimethyl-2,4-piperidindione; 6,6-Dimethyl-2-thioxo-4-piperidone; 4-Hydroxy-6,6-dimethyl-5,6-dihydro-2(1H)-pyridone, and -pyridinethione; Keto-enol-tautomeris m
- Zigeuner, Gustav,Schweiger, Klaus,Fuchsgruber, Alfred
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p. 187 - 198
(2007/10/02)
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